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(S)-(+)-3-Hydroxytetrahydrofuran CAS 86087-23-2

Molecular Formula: C4H8O2

Formula Weight: 88.11

ZSpharmac: (S)-(+)-3-Hydroxytetrahydrofuran Supplement

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Product Name: (S)-(+)-3-Hydroxytetrahydrofuran
CAS No: 86087-23-2  
Purity: 99%

Basic Info

Product Name:(S)-(+)-3-Hydroxytetrahydrofuran
Other Names:(S)-(+)-3-Hydroxytetrahydrofuran
CAS:86087-23-2
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Pharmaceutical Intermediates
Appearance:Clear Colorless to Pale Yellow Liquid
EINECS No.:1308068-626-2
Storage:Keep in Dark Place,Sealed in Dry,Room Temperature
Provide:(S)-(+)-3-Hydroxytetrahydrofuran MSDS;
(S)-(+)-3-Hydroxytetrahydrofuran COA

What is (S)-(+)-3-Hydroxytetrahydrofuran?

(S)-(+)-3-Hydroxytetrahydrofuran is a colorless to pale yellow transparent liquid, which can be used as a detection reagent for chemiluminescence analysis. It is used for the first-line treatment of advanced non-small cell lung cancer and the intermediate of the raw material drug afatinib for patients with HER2-positive advanced breast cancer.

(S)-(+)-3-Hydroxytetrahydrofuran Properties:

alpha 18.5 º (c=2 MeOH)
Boiling point 80 °C/15 mmHg (lit.)
density 1.103 g/mL at 25 °C (lit.)
refractive index n20/D 1.45(lit.)
Fp 175 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
pka14.49±0.20(Predicted)
form Liquid
Specific Gravity1.11
color Clear colorless to pale yellow
optical activity[α]20/D +17.5°, c = 2.4 in methanol
Water Solubility soluble

(S)-(+)-3-Hydroxytetrahydrofuran Uses

  1. The synthesis of the anti-AIDS drug amprenavir requires two important intermediates, one of which is (S)-(+)-3-hydroxytetrahydrofuran. It can be synthesized by asymmetric hydroboration or hydrosilation of dihydrofuran, asymmetric hydrogenation reduction of 4-chloro-3-carbonyl butyrate-intramolecular etherification, enzymatic resolution of 3-hydroxytetrahydrofuran racemate, etc. However, the optical purity of the product is insufficient in most cases.
  2. (S)-(+)-3-Hydroxytetrahydrofuran can be used for the first-line treatment of advanced non-small cell lung cancer (NSCLC) and the intermediate of the raw material drug afatinib for patients with HER2-positive advanced breast cancer. .

Preparation of (S)-(+)-3-hydroxytetrahydrofuran

report one,
A synthetic method of (S)-(+)-3-hydroxytetrahydrofuran, comprising the following steps:
(1) Add 250g (1.86mol) L-malic acid and 500ml methanol into a 1000ml four-neck reaction flask, turn on stirring, add 20g (0.1mol) concentrated sulfuric acid, after the addition of materials, open condensed water, oil bath 75 ℃, under reflux The reaction was carried out for 2 hours, and the sample was sent to the gas phase to detect the completion of the reaction. After cooling to room temperature, sodium carbonate was added to adjust the pH to 8. The methanol was removed under reduced pressure, and 100 ml of water was added. Afterwards, check whether the water phase has been extracted cleanly, if not, extract it once more with 100ml of dichloromethane, combine the organic phases, remove the solvent under reduced pressure, and steam out 277g of L-dimethyl malate, with a yield of 92%;
(2) Add 100ml of tetrahydrofuran into a 500ml four-necked reaction flask, add 4.663g (0.123mol) of sodium borohydride under stirring, open the condensed water, and then slowly drop 10g (0.0617mol) of L-dimethyl malate into the reaction flask In the bottle, the dripping is completed, the oil bath is heated and refluxed, 20 ml of methanol is added dropwise to the reaction solution under reflux, the dripping is completed, the reflux is stirred for 2 hours, the sampling is completed to detect the reaction, and it is cooled to room temperature to obtain a mixed solution, and then 500 ml of anhydrous ethanol is added. In a 1000ml four-neck reaction flask, start stirring, pour the mixture into absolute ethanol, slowly add 15g (0.15mol) phosphoric acid dropwise, stir at room temperature for 25min, filter, and rinse the filter cake with absolute ethanol 3 times, 20ml each time , the organic phases were combined, and the solvent was removed under reduced pressure to obtain 5.8 g of crude chiral 1,2,4-butanetriol with a yield of 90%;
(3) Add the obtained crude chiral 1,2,4-butanetriol into a vacuum distillation device, heat up to 120°C for self-reaction, and steam (S)-(+)-3-hydroxytetrahydrofuran and water under reduced pressure. The mixture was then dehydrated under reduced pressure at a temperature of 76 °C to obtain 2.4 g of (S)-(+)-3-hydroxytetrahydrofuran with a yield of 45% and an optical purity >99% ee (by chiral gas chromatography Sure).
report two,


Preparation of L-dimethyl malate 2: Dissolve 30g L-malic acid (0.224mol) in 90ml methanol, cool to -10°C, add 39ml thionyl chloride (0.55mol) dropwise with stirring, and finish adding dropwise in 1.5h . Stir at room temperature for 4 h, and then heat to reflux for 1 h to stop the reaction. Concentrate under reduced pressure, add 125 ml of 20% sodium carbonate solution to adjust pH=7.Filter three times, 100ml each time The ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 33.68 g of a colorless oily liquid with a yield of 93%.
Preparation of butanetriol 3: 32.4g L-dimethyl malate (0.2mol) was dissolved in 100ml methanol, 8.48g potassium borohydride (0.16mol) and 17g lithium chloride (0.4mol) were added, and the mixture was heated to reflux. Thereafter, 4.24g potassium borohydride (0.08mol) was added every 20min for a total of 5 times. After the addition was completed, reflux was continued for 3h, and no starting material was detected by TLC, and the reaction was stopped. A large amount of solid was removed by filtration first, the filtrate was adjusted to pH 3 with sulfuric acid, the precipitated solid was removed by filtration again, and concentrated under reduced pressure. The resulting solid-liquid mixture was diluted with 20 ml of ethyl acetate and 20 ml of ethanol, stirred and filtered. The filtrate was concentrated under reduced pressure to obtain 21 g of yellow viscous liquid.
Preparation of (S)-(+)-3-hydroxytetrahydrofuran 4: The crude product obtained in the previous step was added to 2 g (0.01 mol) of p-toluenesulfonic acid monohydrate, heated to dissolve, and the temperature was continued to rise to 200°C. Fractional distillation under reduced pressure (87° C./22 mmHg) collected 7.6 g of yellow oily liquid with a two-step yield of 43%.

(S)-(+)-3-Hydroxytetrahydrofuran Hazard Identification GHS Classification

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signal warning
GHS Hazard Statements
H315 (100%): Causes skin irritation [warning skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [WARNING Serious eye damage/eye irritation]
H335 (98.15%): May cause respiratory irritation [WARNING Specific target organ toxicity, single exposure; respiratory irritation]
precautionary statement code
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405 and P501
(The corresponding statement for each P-code can be found on the GHS classification page.)
ECHA C&L Notice Summary
Aggregated GHS information provided by 55 companies to the ECHA C&L List from 6 notifications. Each notification may be associated with multiple companies.
1 in 55 companies reported not meeting GHS hazard criteria. For more details, visit the ECHA C&L website.
In 5 notices provided by 54 of the 55 companies, there are hazard statement codes.
Information may vary between notifications depending on impurities, additives and other factors. Percentage values ​​in parentheses represent the notification classification rate for companies that provide hazard codes. Only hazard codes with a percentage value above 10% are displayed.

Company Profile and Corporate Culture

Company Profile:

ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .

The company’s competitive product is pharmaceutical raw materials and intermediates (especially carbohydrate derivatives Series), In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry .

The company insists on the spirit of “sincere management, strict quality control, customer as god” , get consistent high praise from customers at home and abroad.

Company Culture:
OUR MISSION

Help China Chemicals to benefit the happiness of human life

OUR VISION:Become the most trusted chemical supplier in the world

OUR BUSINESS PHILOSOPHY:Striver – oriented, enrich employees, customer first, deep service, seek development

OUR VALUES:Be prepared for danger in times of peace, forge ahead actively, unity and cooperation, and be brave to fight

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info
  • Business Type: Manufacturer
  • Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
  • Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
  • Total Employees: 51~100
  • Capital (Million US $): 10000000RMB
  • Year Established: 2016
Production Capacity
  • No. of Production Lines : 8
  • No. of QC Staff : 5 -10 People
  • OEM Services Provided : yes
  • Factory Size (Sq.meters) : 3,000-5,000 square meters
  • Certificate: ISO9001 , CE , GMP , API , MSDS
  • Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

Service

Pre-Sales Service

* Prompt reply and 24 hours online, professional team to provide best price and high quality product.

* Sample testing support.

* Every batch of products will be tested to ensureits quality.

*The packing also can be according the customers` requirment.

*Any inquiries will be replied within 24 hours.

*we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate. If your markets have any special requirements, let us know.

 

After-Sales Service

*The fact of logistics information monitoring.

* Any questions about the product can be consulted at any time.

*Product has any problem can return.

FAQ

Do you accept sample order?

We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

 

HOW TO CONFIRM THE PRODUCT QUALITY BEFORE PLACING ORDERS?

You can get free samples for some products,you only need to pay the shipping cost or arrange a courier to us and take the samples. You can send us your product specifications and requests,we will manufacture the products according to your requests.

What’s your MOQ?

Our MOQ is 1kg. But usually we accept less quantity such as 100g on the condition that sample charge is 100% paid.

Do you supply product report?

Yes. We’ll give you product analysis report before shipping.

  Is there a discount?

Different quantity has different discount.

Shipping

1. ≤50kg, Express delivery recommended, usually called as DDU service;

2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;

3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;

4. For high value products, please select air shipping and express delivery for safe.

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